It is known that p-hydroxyaniline derivatives of the formula I ##STR2##
are employed as active compounds in fungicidal compositions. Thus compounds of the formula I are disclosed in EP-A 0 339 481, EP-A 0 653 418 and the German Patent Applications 195 04 599.8 and 95 40 970.1.
EP-A-545 099 describes anilide compounds of the formula ##STR3##
where A is phenyl which is substituted in the 2-position by ethyl, trifluoromethyl, chlorine, bromine or iodine or is certain aromatic or nonaromatic heterocyclic radicals, which can be unsubstituted or substituted by methyl, chlorine or trifluoromethyl, and R is certain aliphatic or cycloaliphatic radicals, which can be unsubstituted or substituted by halogen, or is phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or halogen. These compounds can be used for controlling Botrytis.
EP-A-589 301 describes anilide compounds of the same formula, where A is a cyclic radical of the formula: ##STR4##
where R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl; R.sup.2 is halogen or C.sub.1 -C.sub.4 -alkyl; R.sup.3 is C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl; n is 1 or 2; and R essentially has the meanings indicated above. These compounds can also be used for treating Botrytis.
WO 93/11117 describes compounds of the formula ##STR5##
where
Q is C.sub.1 -C.sub.3 -alkyl, C.sub.2 -C.sub.3 -alkenyl, C.sub.2 -C.sub.3 -alkynyl, --(CH.sub.2).sub.m CH.dbd. or --(CH.sub.2).sub.m --X--(CH.sub.2).sub.m --; PA1 n is 0 or 1; PA1 each m independently of one another is 0, 1, 2 or 3; PA1 each X independently is O or S; PA1 R.sup.1 is certain alicyclic radicals; PA1 R.sup.2 is hydrogen, fluorinated methyl, methyl, ethyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -chloroalkyl, phenyl, alkylthioalkyl, alkoxyalkyl, haloalkylthioalkyl, haloalkoxyalkyl or hydroxyalkyl; PA1 R.sup.3 is halomethyl, halomethoxy, methyl, ethyl, halogen, cyano, methylthio, nitro, aminocarbonyl or aminocarbonylmethyl; PA1 R.sup.4 is hydrogen, halogen or methyl; PA1 R.sup.5, R.sup.6 and R.sup.7 are each independently of one another selected from hydrogen, halogen, cyano, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.3 -C.sub.4 -cycloalkyl and halomethoxy. These compounds are fungicidally active, but on their own do not have a sufficiently broad and satisfactory spectrum of action. PA1 a) at least one p-hydroxyaniline derivative of the formula I ##STR6## PA1 R.sup.1 is hydrogen, alkyl, which can be partially or completely halogenated and/or can carry one or two of the following groups: alkoxy, haloalkoxy, alkylthio, cycloalkyl, cycloalkenyl, it being possible for the cyclic groups for their part to carry one, two or three halogen atoms, alkyl groups and/or alkoxy groups, and aryl which can be partially or completely halogenated and/or can carry one, two or three of the following substituents: nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio; PA1 cycloalkyl or cycloalkenyl, it being possible for these radicals to be partially or completely halogenated and/or to carry 1, 2, 3, 4 or 5 of the following groups: alkyl, haloalkyl, alkoxy, haloalkoxy and aryl, which can be partially or completely halogenated and/or can carry one, two or three of the following substituents: nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio; PA1 C.sub.6 -C.sub.15 -bicycloalkyl or C.sub.7 -C.sub.15 -bicycloalkenyl, it being possible for these radicals to be partially or completely halogenated and/or to carry 1, 2, 3, 4 or 5 of the following groups: alkyl, haloalkyl, alkoxy, haloalkoxy and aryl, which can be partially or completely halogenated and/or can carry one, two or three of the following substituents: nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio; PA1 R.sup.2 and R.sup.3 independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy; PA1 z is H or R.sup.4 --(CO)--, where PA1 R.sup.4 is the following radicals: alkyl or alkenyl, it being possible for these groups to be partially or completely halogenated and/or to carry one of the following radicals: alkoxy, haloalkoxy, alkylthio, cycloalkyl, cycloalkenyl or aryl, it being possible for the aromatic radicals for their part to carry one, two or three of the following groups: nitro, cyano, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio; PA1 cycloalkyl or cycloalkenyl, it being possible for these groups to carry one, two or three of the following radicals: halogen, alkyl, haloalkyl and alkoxy; PA1 aryl, which can be partially or completely halogenated and/or can carry one, two or three of the following radicals: nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio; PA1 OR.sup.5 or NR.sup.6 R.sup.7, where PA1 R.sup.5 is alkyl or alkenyl, it being possible for these groups to be partially or completely halogenated and/or to carry one of the following radicals: alkoxy, haloalkoxy, alkylthio, cycloalkyl, cycloalkenyl or aryl, it being possible for the aromatic radicals for their part to carry one, two or three of the following groups: nitro, cyano, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio; PA1 or is cycloalkyl or cycloalkenyl, it being possible for these groups to carry one, two or three of the following radicals: halogen, alkyl, haloalkyl and alkoxy; PA1 or is aryl which can be partially or completely halogenated and/or can carry one, two or three of the following radicals; nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio; PA1 R.sup.6 is alkyl or alkenyl, it being possible for these groups to be partially or completely halogenated and/or to carry one of the following radicals: alkylthio, cycloalkyl, cycloalkenyl or aryl, it being possible for the aromatic radicals for their part to carry one, two or three of the following groups: nitro, cyano, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio; PA1 cycloalkyl or cycloalkenyl, it being possible for these groups to carry one, two or three of the following radicals: halogen, alkyl, haloalkyl and alkoxy; PA1 aryl, which can be partially or completely halogenated and/or can carry one, two or three of the following radicals: nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio; and PA1 R.sup.7 is hydrogen or alkyl, and PA1 b) at least one amide compound of the formula II EQU A--CO--NR.sup.8 --R.sup.9 (II) PA1 A is an aryl group or an aromatic or nonaromatic, 5- or 6-membered heterocycle which has 1 to 3 heteroatoms which are selected from O, N and S; it being possible for the aryl group or the heterocycle, if appropriate, to have 1, 2 or 3 substituents which are selected independently of one another from alkyl, halogen, CHF.sub.2, CF.sub.3, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl and alkylsulfonyl; PA1 R.sup.8 is a hydrogen atom, alkyl or alkoxy; PA1 R.sup.9 is a phenyl or cycloalkyl group which, if appropriate, has 1, 2 or 3 substituents which independently of one another are selected from phenyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkenyl, cycloalkyloxy and cycloalkenyloxy, and which can additionally be substituted by 1 or more halogen atoms, it being possible for the aliphatic and cycloaliphatic radicals to be partially or completely halogenated and/or the cycloaliphatic radicals to be substituted by 1, 2 or 3 alkyl groups and for the phenyl group for its part to have 1 to 5 halogen atoms and/or 1 to 3 substituents which independently of one another are selected from alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and haloalkylthio, and the amide phenyl group, if appropriate, being fused to a saturated 5-membered ring which, if appropriate, is substituted by 1 or more alkyl groups and/or can have a heteroatom selected from O and S. PA1 Z is hydrogen; PA1 R.sup.1 is alkyl, which can be partially or completely halogenated and/or can carry one or two of the following groups: alkoxy, haloalkoxy, cycloalkyl, cycloalkenyl, it being possible for the cyclic groups for their part to carry one, two or three halogen atoms and/or alkyl groups, and aryl, which can be partially or completely halogenated and/or can carry one, two or three of the following substituents: alkyl and haloalkyl; PA1 cycloalkyl or cycloalkenyl, it being possible for these radicals to be partically or completely halogenated and/or to carry 1, 2, 3, 4 or 5 of the following groups: alkyl, haloalkyl and aryl, which can be partially or completely halogenated and/or can carry one, two or three of the following substituents: alkyl and haloalkyl; PA1 C.sub.6 -C.sub.15 -bicycloalkyl or C.sub.7 -C.sub.15 -bicycloalkenyl, it being possible for these radicals to be partially or completely halogenated and/or to carry 1, 2, 3, 4 or 5 alkyl or haloalkyl groups; PA1 R.sup.2 and R.sup.3 independently of one another are halogen, alkyl and haloalkyl. PA1 Z is hydrogen; PA1 R.sup.1 is alkyl which can be partially or completely halogenated and/or can carry aryl, which for its part can be partially or completely halogenated and/or can carry alkyl; PA1 cycloalkyl or cycloalkenyl, it being possible for these radicals to be partially or completely halogenated and to carry 1, 2, 3, 4 or 5 alkyl groups; PA1 bicycloalkyl or bicycloalkenyl, it being possible for these radicals to be partially or completely halogenated and/or to carry 1, 2, 3, 4 or 5 alkyl groups; PA1 R.sup.2 and R.sup.3 independently of one another are halogen, in particular fluorine or chlorine, or alkyl. PA1 phenyl, pyridyl, dihydropyranyl, dihydrooxathiinyl, dihydrooxathiinyl oxide, dihydrooxathiinyl dioxide, furyl, thiazolyl, pyrazolyl or oxazolyl, it being possible for these groups to have 1, 2 or 3 substituents which independently of one another are selected from alkyl, halogen, difluoromethyl and trifluoromethyl. PA1 pyridin-3-yl, which is unsubstituted or substituted in the 2-position by halogen, methyl, difluoromethyl, trifluoromethyl, methoxy, methylthio, methylsulfinyl or methylsulfonyl; PA1 phenyl which is unsubstituted or substituted in the 2-position by methyl, trifluoromethyl, chlorine, bromine or iodine; PA1 2-methyl-5,6-dihydropyran-3-yl; PA1 2-methyl-5,6-dihydro-1,4-oxathiin-3-yl or the 4-oxide or 4,4-dioxide thereof; PA1 2-methylfuran-3-yl, which is unsubstituted or substituted in the 4- and/or 5-position by methyl; PA1 thiazol-5-yl, which is unsubstituted or substituted in the 2- and/or 4-position by methyl, chlorine, difluoromethyl or trifluoromethyl; PA1 thiazol-4-yl, which is unsubstituted or substituted in the 2- and/or 5-position by methyl, chlorine, difluoromethyl or trifluoromethyl; PA1 1-methylpyrazol-4-yl, which is unsubstituted or substituted in the 3- and/or 5-position by methyl, chlorine, difluoromethyl or trifluoromethyl; or PA1 oxazol-5-yl, which is unsubstituted or substituted in the 2- and/or 4-position by methyl or chlorine. PA1 C.sub.3 -C.sub.6 -alkyl, C.sub.5 -C.sub.6 -cycloalkenyl, C.sub.5 -C.sub.6 -cycloalkyloxy, C.sub.5 -C.sub.6 -cycloalkenyloxy, it being possible for these groups to be substituted by 1, 2 or 3 C.sub.1 -C.sub.4 -alkyl groups, PA1 phenyl, which is substituted by 1 to 5 halogen atoms and/or 1 to 3 groups which independently of one another are selected from C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -haloalkylthio, PA1 indanyl or oxaindanyl, which is unsubstituted or substituted by 1, 2 or 3 C.sub.1 -C.sub.4 -alkyl groups. PA1 A is ##STR16## PA1 X is methylene, sulfur, sulfinyl or sulfonyl (SO.sub.2), PA1 R.sup.10 is methyl, difluoromethyl, trifluoromethyl, chlorine, bromine or iodine, PA1 R.sup.11 is trifluoromethyl or chlorine, PA1 R.sup.12 is hydrogen or methyl, PA1 R.sup.13 is methyl, difluoromethyl, trifluoromethyl or chlorine, PA1 R.sup.14 is hydrogen, methyl or chlorine, PA1 R.sup.15 is methyl, difluoromethyl or trifluoromethyl, PA1 R.sup.16 is hydrogen, methyl, difluoromethyl, trifluoromethyl or chlorine, PA1 R.sup.17 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or halogen. PA1 R.sup.18 is halogen and PA1 R.sup.19 is phenyl which is substituted by halogen. PA1 I. a solution of 90 parts by weight of the active compounds and 10 parts by weight of N-methylpyrrolidone, which is suitable for application in the form of very small drops; PA1 II. a mixture of 20 parts by weight of the active compounds, 80 parts by weight of xylene, 10 parts by weight of the addition product of from 8 to 10 mol of ethyleneoxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 5 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil; by finely dispersing the solution in water a dispersion is obtained; PA1 III. an aqueous dispersion of 20 parts by weight of the active compounds, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition products of 40 mol of ethylene oxide to 1 mol of castor oil; PA1 IV. an aqueous dispersion of 20 parts by weight of the active compounds, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280.degree. C. and 10 parts by weight of the addition product of 40 mol of ethylene oxide to 1 mol of castor oil; PA1 V. a mixture, ground in a hammer mill, of 80 parts by weight of the active compounds, 3 parts by weight of the sodium salt of diisobutylnapthalene-1-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel; by finely dispersing the mixture in water a spray mixture is obtained; PA1 VI. an intimate mixture of 3 parts by weight of the active compounds and 97 parts by weight of finely divided kaolin; this dusting composition contains 3% by weight of active compound; PA1 VII. an intimate mixture of 30 parts by weight of the active compounds, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil, which has been sprayed onto the surface of the silica gel; this preparation gives the active compounds a good adherence; PA1 VIII. a stable aqueous dispersion of 40 parts by weight of the active compounds, 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which can be further diluted; PA1 IX. a stable oily dispersion of 20 parts by weight of the active compounds, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 88 parts by weight of a paraffinic mineral oil.
When these active compounds are used alone, however, it has been shown that their action is only temporary, i.e. after some time renewed growth of the fungi could be observed.